Chemical resolution and racemization of 1,2- and 3,4-epoxydihydrophenanthrene

Abstract
1,2- and 3,4-Epoxy-1,2,3,4-tetrahydrophenanthrene were each separable into enantiomers while the corresponding 1,2- and 3,4-epoxydihydrophenanthrene (derived from identical chiral precursors) showed evidence of spontaneous racemization; preliminary PMO calculations indicate that oxepin intermediates could account for this configurational instability.

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